Diethyl Ether → 1-(4-Bromo-2-(methoxymethyl)phenyl)-2-methylpiperidine

HRID 219872

反応式

HRID 219872 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH3:16])=[C:6]([CH2:8][OH:9])[CH:7]=1.[CH2:17](N(C(C)C)C(C)C)C.CS(Cl)(=O)=O.CCOCC>C(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH3:16])=[C:6]([CH2:8][O:9][CH3:17])[CH:7]=1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58554197(5-Bromo-2-(2-methylpiperidin-1-YL)phenyl)methanol

生成物 1

HCID 585541231-(4-Bromo-2-(methoxymethyl)phenyl)-2-methylpiperidine収率 156.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

To a solution of solution of [5-bromo-2-(2-methylpiperidin-1-yl)phenyl]methanol (7.9 g; 27.8 mmol) and n-ethyldiisopropylamine (10.40 mL; 61.15 mmol) in anhydrous DCM (150 mL) cooled to 0° C., was added methanesulfonyl chloride (2.36 mL; 30.57 mmol). The reaction mixture was diluted with MeOH (150 mL) and heated to 50° C. for 3 h after which time solvents were removed under vacuum to give a brown oil. Residue was taken up with Et2O (450 mL), washed with water (150 mL, pH 8 adjusted with aqueous NaOH), saturated aqueous solution of NH4Cl (2×150 mL) and brine (150 mL). The combined organic layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure to give the title compound as a brown yellow oil (12.97 g, 92%). LC/MS (Method B): 298.1 (M+H)+.

後処理

  1. customwere removed under vacuum
  2. customto give a brown oil
  3. washwashed with water (150 mL, pH 8 adjusted with aqueous NaOH), saturated aqueous solution of NH4Cl (2×150 mL) and brine (150 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-e44ed2c331294eb89cf18ac3e1d755e3
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

関連ノート

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